Skip to content
qorganica.es qorganica.comOrganic Chemistry made transparent Course map Español

SolutionsReactivity

1. One reagent, many products

Give the product of propanoyl chloride with: a) H2O; b) ethanol and pyridine; c) two equivalents of diethylamine; d) (CH3)2CuLi; e) LiAl(O-t-Bu)3H; f) benzene and AlCl3.

  1. Propanoic acid.
  2. Ethyl propanoate.
  3. N,N-Diethylpropanamide (and diethylammonium chloride).
  4. 2-Butanone.
  5. Propanal.
  6. Propiophenone (1-phenyl-1-propanone).

2. Why not Grignard?

Why is CH3MgBr not used to obtain a ketone from an acid chloride?

The Grignard reagent is so reactive that it also attacks the ketone formed, leading to a tertiary alcohol. Cuprates are milder and stop at the ketone.

← Back to the exercises